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Going Against the Crowd

Updated: Oct 4, 2021

An interview with Jes Bailey, digital nomad and founder of Crowdfund 360, by Elizabeth Harris.

Jes Bailey, digital nomad and founder of Crowfund 360, giving a presentation on crowdfunding. Interview for Toastee Mag
Jes Bailey, digital nomad and founder of Crowfund 360, giving a presentation on crowdfunding.

Crowdfunding has become such a phenomenon. Being a digital nomad is now one of the dream careers. Behind these trends are a lot of hard work and thought.

I spoke with Jes Bailey. Jes is the founder of Crowdfund 360 which focuses on coaching, training, and supporting crowdfunding campaigns for both startups and third sector organizations. She’s even conducted training sessions for the UN and EU!

Because her work takes her everywhere and she can work from anywhere, before the pandemic, Jes was living the digital nomad life, traveling across Europe and working pretty much anywhere her heart desired.

I talked with Jes about crowdfunding, living a modern nomadic life, and their hard realities.

Jes, can you start by telling our Toastee Audience a little about how you began in the arena of crowdfunding?

Before starting Crowdfund 360, I worked in Human Rights and International Development and I thought I wanted to be a human rights lawyer. My undergraduate degree was in Geography and International Development, and I wanted to work in the field for a bit before I committed to a Masters. As much as I liked human rights law, I realized I was never going to be one of those stereotypical lawyers - I like wearing jeans and flip flops and I don’t like mornings, I don’t like dressing up in ‘office attire’. I like hula hooping and surfing in my spare time!

I was working in the Hague (the Netherlands), on a human rights project in Bangladesh and got frustrated wondering if the work was actually doing anything, or were we just spending all our time chasing EU money. I went out to Bangladesh, and thought, you can change the law, but bad people are still going to do bad things. We were working to get street kids out of jail. They get rounded up on the streets, put in jail, and are forgotten about until they are 18, as they are not in any systems. We used to go into the jails, identify the street kids and try to figure out where they had come from. From this, I thought it's not the law that needs to change, it's the awareness.

I like graphic design as well as the academic paper side of studying, so felt communications was a more suitable field of study to pursue and began looking at masters in the political and communications sector. There was one Masters in Political Communications in Amsterdam, and as I was already living in Holland, where it was 10 times cheaper than the one in London for Human Rights law! Amsterdam is the best place in Europe for communication science, and I thought that's the one for me. Because of the work I had been doing in the charity sector, I did my thesis and all my research on the non-governmental sector rather than the political sector. My thesis was about interactivity and charitable giving.

Say for example I see a charity advert in a newspaper, a video ad, or an ad in an app, my research was asking does it affect how likely people are to give money and does that affect how much money people give. This would help charities understand how best to raise money from individual people. Obviously, that's quite linked to crowdfunding!

After my Master’s, I applied for three jobs, one in Bangladesh, one in Holland, and one in London. The one in London was at a crowdfunding platform, and the others were in the social enterprise/charity sector. I thought to myself, this crowdfunding thing seems cool because it’s related to my thesis. I have never lived in London and it had been 6 years since I was back in the UK, so wanted to give that a go. I’d done Holland, I’d done Bangladesh, let's see what London is like!

Jes running a crowdfunding workshop at a startup center. Crowdfun 360 workshop
Jes running a crowdfunding workshop at a startup center.

I handed my thesis in on a Friday and started the job on Monday, so I had one weekend to pick everything up and move back to the UK. It was a rollercoaster, but I loved it. I went all around England training small charities on crowdfunding and teaching workshops. I taught an online course to charities all across the world about how to crowdfund. I loved it and thought this is what I want to do.

My contract came to an end and I went to all the other platforms and asked for a job. Back in 2016, none of the platforms hired anyone to help organizations succeed - which is ridiculous! The Head of Europe at Indiegogo and I met for a coffee (I was asking for a job) and he told me I’d never get hired by a platform. They have too many campaigns and that I should go set up my own business because people needed what I was doing.

At the time, I never thought I’d set up a business. I always thought I’d work in the charity sector. I carried on applying for other jobs in PR, Comms- but this niggle in the back of my mind kept telling me if I don’t take this chance now, when am I going to in the future? At that point I had really low rent, living with some family members, I didn’t have any dependents, no worries with life. If it all went wrong, that was a great time for it to all go wrong! l I wasn’t going to lose much, I was the only one starving at the end of the day. And that was 4 years ago.

Congratulations on making it 4 years in the game! How has it been building the business?

The beginning was relatively easy. I think for a lot of people the beginning is easier because it's the time when everyone is enthusiastic and wants to support you. It’s the time when all your friends share your website, there is support from incubators, networks, and there are a lot of workshops and webinars for new businesses.

I was lucky in that crowdfunding was a known thing, and I already had clients lined up and ready for when I left my previous role. After the first 6 months, the excitement of a new business and we want to help you’s wear out.

Crowdfunding is very seasonal. It's really hard to raise money in the summer, and again in the December and January period. In the summer everyone is on holiday and not thinking about looking at a computer screen. In December-January everyone is thinking about Christmas. My 6-month mark coincided with summer and all my first clients' fundraising campaigns ended, but no one was interested in signing up to do it again. People might want to raise money in September, but they’re not necessarily thinking about it in July, they’re still on holiday mode.

I started questioning my decision to start a business, I had no income, no clients- it's a complete disaster! September came around and it went straight back up. So the next year, I knew it was going to be bad in the summer. Even in an average month, the last week is the hardest as everyone is waiting to get paid, but the first week is great because everyone has got paid. Even during the week, Tuesdays and Wednesdays are the best days to launch a campaign, because everyone is procrastinating at work. Friday and Sunday are the worst days as everyone is too busy thinking about work and doesn't want to look at a computer screen.

Jes Bailey of Crowdfund 360 running a crowdfunding session.
Jes running a crowdfunding session.

I’ve also worked in the Charity Sector, and I wanted to ask about your experience. There are misconceptions about when you fundraise and raise money, and how this can help support the charity.

There are loads of misconceptions. The biggest misconception small charities can’t run big crowdfunding campaigns, but actually small charities and organizations do better at crowdfunding than big ones because they have a face and a personality.

Crowdfunding needs every person in the organization to be involved. If the founder doesn’t care, if the operations manager doesn't use their network, it won't work. A lot of other people just see the task of fundraising as a task for the fundraiser’s role, but they all need to work as a team. A lot of my early work is talking with the entire team to get everyone to buy into this.

The other big issues are time and resources. A lot of the roles are part-time, they have other things to do. Crowdfunding is 24/7 once you get into it. You get pledges every day, you need to update every day, and as much as you can schedule these things, a lot of the other things happen like getting a request for a radio interview or a TV promo for a campaign. You can't say "No, sorry I don’t work on Tuesdays." That is not going to be good for your campaign. PR like this can really blow up the project.

The biggest misconception about crowdfunding is that people just want to give you money. The number of emails I get that saying, "I want to raise a million pounds but I don’t have an email list or a social media following." No one is going to come and run towards you and buy it if they haven’t heard what you’re doing. If you go out into the street and ask for money, people are going to ignore you. It's The same online, most people are going to ignore you. Emails have a conversion rate of 25% whereas a Facebook post has a conversion rate of only 4% - imagine how big your following would need to be if you relied only on social media.

We always have a minimum of 2 months of preparation. Once you click live, there is no going back. We all know that first impressions are key. If people come to me halfway through a campaign looking for it to be saved, it is a lot of hard work as there may already be a sour taste in the audience’s mouth. We’re not starting at a neutral level, we're starting in a negative zone and trying to bring people up to positive which is very hard.

It's all about the preparation work and spending as much time and resources and effort as possible to make sure that prep work is going to work. When the campaign is live, you have 5 weeks of emails ready and the social media posts ready beforehand. All that’s changing on the halfway email is how much money has been raised. When the campaign is live, it's much more important to be having phone calls and coffee meetings where possible with people who would be giving you larger amounts of money because no one is going to give you a larger sum of money after reading an email- they want to meet you, talk to you, face to face, have a chat about the plans, brainstorm, do their due diligence. If there is no time for that because emails are being written or you're creating social media posts then that investment is most likely lost. The preparation is there to make the campaign as smooth as possible.

I always tell people, if you just want the money don’t bother crowdfunding because it is so much work. But if you want to grow your email list, increase your social media following and the engagement that you get with them, if you want to get PR and press coverage, if you want to build up a little pool of ambassadors or volunteers that are super pro your organization, if you want to use the successful campaign in future funding bids or for future investment to show that you can get that many customers or donors in 35 days, then it’s worth it. But if you just need a one-off sum, then there are going to be easier ways to find that money.

Jes Baily of Crowdfund 360 with her bags living the digital nomad life.
Jes with her bags living the digital nomad life.

Jes you used to travel all around Europe and beyond giving presentations and training sessions. Would you describe yourself as a digital nomad?

Not at the moment. Pre-pandemic in 2018, yes I was in 12 countries and took 17 flights. In 2019 I decided not to catch an airplane. It felt like I’d spent all of 2018 in the airport, I needed a break. I got a camper van with solar power so I could drive and work. At the end of 2018, I had been so sick of living out of Airbnb, I wanted to have my own space, a base that I could travel from.

It’s not as glamorous. I remember in October 2018 I woke up one morning in a hotel in the North of England, and I just thought to myself, "I don’t know where I am, what city am I in again?" It had been a crazy month where I had been in different cities in England, Scotland, and Germany in one month, it was ridiculous. I woke up thinking, "I think I’m in England. I think, but it could be Scotland, but I don’t remember what city I’m in." It took me some time to remember, and it threw me all day, I felt so disjointed.

I don’t think people talk about the flip side of it enough because you get so used to it, and it’s so idealized on Instagram and all those things. The reality is it can be really hard.

From 2016 to now, what are some of the ups and downs?

The biggest ups have been looking back on it and seeing how far I’ve come. I did not think I'd be in the position to have my own business. No one in my family went to university, I’m the only person in my family to have left the country, the second to have left our town, so I

went outside the box!

I didn’t know it would go as well as it has. I’ve managed to buy a house, on my own after 3 years. Looking back now and thinking about 2016 Jes, if I had known what was coming for me, I don’t think I would have believed it. The opportunity to live a life I want to live, travel where and when I want, for however long I want. There have been times in the 4 years where I’ve questioned why I chose this, if my life would be better if I’d taken a more traditional trajectory, but, right now I wouldn’t change it. I’m thankful for 2016 Jes for being brave and taking that jump, it was a good decision.

But, there are downs. If you get sick when self-employed, it’s really hard. 2019 was not a good year for me. I threw myself into work and I paid for that later on. I live far from family members, and I have to earn money to pay rent. This year I also injured my neck and I could not work as much as I wanted to. I don’t have that safety net as much as in a typical job.

The upsides are that I did a workshop for the UN, I was on BBC radio, I traveled to over 20 countries doing crowdfunding workshops. My best friend is in LA, so I don’t get to see her, but I went to LA for a month and worked there. She had to go to Portugal, so I just went there for a month because I could. So having that freedom makes it worth it.

Jes Bailey of Crowdfund 360 at the UN after running a crowdfunding sessions with them.
Jes at the UN after running a crowdfunding sessions with them.

What advice would you have for our readers who want to start their own business and venture out on their own?

You’re never going to know enough so just do it. Know some stuff, but research where you want to go, where you’d like to live, and if there is internet service. You’ll never know everything, but you’ll never think you’re ready enough to launch.

Another bit of advice is don't jump in the deep end straight away. Wind down your current role, going full-time to part-time, build the idea up- the website, the logo, the blog articles, the YouTube videos. Build your offering to a point where you’re ready to sell with customers. I built my first online course over the Christmas break in 2016 so when January 1st came, I knew I had a product to sell to everyone else.

What's next for you Jes?

I’ve just launched a new course on how to build a crowd to help those in the really early days of launching a business. It is about targeting people before even thinking about crowdfunding, before launching a new product. It covers building a landing page that's going to convert into email addresses, building a mail chimp funnel, building a social media following, and finding your target market so that you are ready to crowdfund and you have an engaged audience of customers ready. I’ll focus on this for the first half of this year, and see if it's a good offering.

I’m also working on my clients, keeping my success rate high, and educating people that crowdfunding is a lot of work. We do a lot of youtube videos with people who have crowdfunded to talk about the ups and downs, to talk about what worked and what didn’t to share with people who want to crowdfund.

Inspired to learn more about crowdfunding and plan a crowdfunding campaign, check out Jes’ company Crowdfund 360 at You can find resources and her crowdfunding services there.

Make sure to keep up to date with Jes and Crowdfund 360 by following her on social @crowdfund360 on Twitter and @jes_crowdfund360 on Instagram.

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